In the end, they finally got the clutch hit.
When Matt Wieters came to the plate with runners on second and third and two outs in the bottom of the tenth, the O's trailed the White Sox 3-2 and they were 1-for-17 with runners in scoring position for the day.
But Wieters delivered a two-run, walk-off single to right and the O's frustrating day ended with a win, 4-3 over Chicago.
The Orioles have their first three-game winning streak since Aug. 6-9 and improve to 76-65 while the White Sox have now lost nine in a row. It was also just the O's second one-run win in their last 11 such decisions.
The White Sox had taken a 3-2 lead in the top of the 10th as pinch-hitter Conor Gillaspie hit a solo homer to right off Tommy Hunter to break the 2-2 tie.
Earlier, the Orioles took a 1-0 lead in the first inning on a Chris Davis RBI double. With his 124th RBI, he moved into a tie for fourth most with Eddie Murray (1985) on the O's single list. Still ahead of him are Jim Gentile (141 in 1961), Rafael Palmeiro (142 in 1996) and Miguel Tejada (150 in 2004).
Chicago moved ahead 2-1 on Wei-Yin Chen with single runs in the fourth and fifth innings before the Orioles tied it 2-2 in the fifth on Brian Roberts' fifth homer. At that point, 18 of the last O's 20 runs had come via a home run.
Chen did not get a decision, but threw six innings allowing six hits and two runs with no walks and eight strikeouts.
This game seemed destined to end as one of the most frustrating of the 2013 season, but instead Wieters clutch hit sent the crowd home happy and the Orioles can sweep the four-game series on Sunday.